Therapeutic compound for pain and synthesis thereof
AssigneeJanssen Pharmaceutica NV
InventorsBart DeCorte, Jacob Cornelis Russcher, Menno Cornelis Franciscus Monnee
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Abstract
The invention provides compounds of Formula XXIII: wherein R1 is hydrogen, alkyl, acyl, or silyl, R2 is hydrogen, alkyl, benzyl, acyl, or ester, and R3 is hydrogen, alkyl, an aromatic group, azacyclic, carbocycle, aryl, cycloalkyl, heterocycloalkyl, heterocycle, heteroaryl, heteroalkyl, acyl, or ester, as well as derivatives and stereoisomers, pharmaceutically acceptable salts and derivatives thereof; and methods of making and using such compounds. The invention includes pharmaceutical compositions containing such compounds, and the use of such compounds in methods of treating conditions, diseases, or disorders.
Claims28
A compound of Formula XXIII(A):
- wherein R2 is selected from the group consisting of hydrogen, C(O)R′ wherein R′ is CH2OCH3, or pyridine optionally substituted with halo;
- wherein R3 is selected from the group consisting of hydrogen, BOC, optionally substituted phenyl, or methylbenzodioxole;
- and
- wherein R4 is hydrogen, alkyl, or cycloalkyl, or a stereoisomer, pharmaceutically acceptable salt, or mixture thereof.
A compound of Formula XXIII(B):
- wherein R1 is selected from the group consisting of hydrogen, benzyl, tert-butyldiphenylsilyl, or C═OR4, wherein R4 is alkyl;
- wherein R3 is selected from the group consisting of hydrogen, BOC, phenyl substituted with CON(R′)2 wherein R′ is H, or;
- and
- wherein R5 is hydrogen, alkyl, alkyl substituted with OCH3, optionally substituted pyridine, or a stereoisomer, pharmaceutically acceptable salt, or mixture, thereof.
A compound of Formula XXIII(D):
- wherein R1 is hydrogen, C═Oalkyl, or C═O cycloalkyl;
- wherein R2 is C═O optionally substituted pyridine or COCH2OCH3;
- and
- wherein R6 is phenyl substituted with CON(R′)2 wherein R′ is H, methylbenzodioxole, azacyclic, pharmaceutically acceptable salt, or mixture thereof.
A compound having the
- or pharmaceutically acceptable salt, or stereoisomer thereof.
A method of producing a compound of
- or
- wherein R1 is hydrogen, tert-butyldiphenylsiyl, or COC3cyloakyl;
- wherein R2 is C═O optionally substituted pyridine, or COCH2OCH3;
- wherein R5 is fluoropyridine or CH2COCH3;
- and
- wherein R3 or R6 is hydrogen, BOC, methylbenzodioxole, or phenyl substituted with CON(R′)2 wherein R′ is H,
- or a stereoisomer, or pharmaceutically acceptable salt thereof, by reacting scopolamine or a derivative thereof.
A compound of Formula XVIII:
- or a stereoisomer, pharmaceutically acceptable salt, or mixture thereof.
Dependencies are inferred from the claim text.